Location: Sarasota , 34231
Do Not Show Listings
2609 WOODGATE LN #K4, SARASOTA, FL 34231
$159,90061 Days on yellowkey MLS ID: N6143915
REDUCED by $5,000 (3.0%) on 06/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1100 Built: 1982Monthly Fee: $588 Tax: $2,358 (2025)Community: Pinewood Village IxCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,358
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: You're five miles from one of the best beaches in America. You just didn't know you could afford to live this close. Ground floor, pool-facing, fully furnished 2BR/2BA in Pinewood Village. Walk out your lanai and you're at the pool. Walk out the front door and Siesta Key Beach, St. Armands Circle, Marina Jack, and downtown Sarasota are minutes away. The best-priced unit in the community — and better than anything else available right now. Ground floor instead of stairs. Tile throughout instead of carpet. Fully furnished and move-in ready the day you close. The only comparable unit in this section spent 385 days on the market and just went pending. This one won't last that long. Flood Zone X. No flood insurance required — a real financial advantage in today's Sarasota market. Outside your door, Sarasota delivers everything. Sarasota Memorial Hospital three miles away. Phillippi Estate Park around the corner. The Van Wezel, the Asolo, the Ringling, the Opera — ten minutes from your front door. The restaurants, the boutiques of St. Armands, the farmers markets, the sailing — all of it yours. Pinewood Village itself overdelivers at this price. Heated pool, fitness center, sauna, shuffleboard, full clubhouse with kitchen. HOA covers cable, water, sewer, trash, pest control, exterior maintenance and building insurance. Phillippi Shores Elementary, Brookside Middle, Riverview High. Association approval required. Sold As-Is. Seller motivated.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Jeffery K. Twigg, Pa (941-412-6505)
2222 FLORINDA ST, SARASOTA, FL 34231
$299,99920 Days on yellowkey MLS ID: A4693347
3 Days Off yellowkey (back on 6/1/2026)
Bed: 2 Bath: 1.0 Gar: 2 Liv Area Sq Ft: 871 Built: 1929 Tax: $2,017 (2025)Community: Tamiami TerraceSingle Family
Taxes:$2,017
Remarks: Under contract-accepting backup offers. This charming Florida cottage sits on a spacious corner lot with no HOA and is full of character and warmth. Featuring a durable metal roof, beautiful hardwood floors, and a cozy wood-burning fireplace, this inviting home blends classic charm with everyday comfort. Natural light pours into the living area through multiple oversized windows, creating a bright and airy atmosphere throughout the home. The open-concept kitchen includes a breakfast bar, stove, dishwasher, and washer/dryer space, making it both functional and welcoming. A split-bedroom layout provides added privacy for guests, while the oversized bathroom offers extra convenience and comfort. Outside, the property includes a 20’ x 20’ two-bay garage along with an additional 10’ x 10’ storage shed. Next to the garage is a separately fenced area ideal for pets, recreational vehicles, boats, or extra outdoor space for entertaining and play. Conveniently located north of Proctor Rd. near School Ave., this home is within walking distance to highly rated Phillippi Shores Elementary School and only minutes from Siesta Key Beach and Downtown Sarasota. A truly appealing home with location, charm, and flexibility all in one package.
Listing is courtesy of: EXP REALTY, LLC (941-462-3321)
Listing Agent: Jennifer Kenna (941-253-3003)
2486 BREAKWATER CIR, SARASOTA, FL 34231
$587,00065 Days on yellowkey MLS ID: A4689678
1 Days Off yellowkey (back on 5/16/2026)
REDUCED by $12,000 (2.0%) on 05/12/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1474 Built: 1966Monthly Fee: $6 Tax: $4,204 (2025)Community: Gulf GateSingle Family
Taxes:$4,204
Elementary School: Gulf Gate Elementary
Remarks: Under contract-accepting backup offers. Price Improvement! A newly imagined Gulf Gate Estates Gem RENOVATED and MOVE-IN READY! Updated to modern specifications this Bright & Fresh home features an inviting floor plan that offers a seamless connection between all living areas, ideal for everyday living and entertaining ~ The Stunning Kitchen Renovation serves as a central gathering space with a large Breakfast Bar (seating for 5) flowing naturally to the Dining & Family Room space that overlooks your Private Backyard Tropical Oasis ~ A separate Living room offers an intimate retreat to enjoy media, conversation or just reading that novel ~ Two distinct Master bedrooms, both w large Walk-In Closets & Ensuite Baths, will suit a variety of lifestyle needs ~ High-impact grade LOW-E Argon windows & doors throughout this home enhance your peace of mind while contributing to energy efficiency and natural light ~ A rare Oversized 1400 sqft screened Pool Cage deck has an insulated covered lanai and overlooks the beautiful PRIVATE tropically landscaped backyard. Relax or entertain as you wish, this is truly an OASIS. ~ Many UPGRADES including: ROOF '25, 3 Ton HVAC & Attic Ducting '23 (10yr transferable warranty), Both Baths Updated '20-23, Kitchen Gutted & Rebuilt w Oversized Quartz Countertop, backsplash, plumbing, wiring, and new wood soft close cabinets '22: ~ Stainless Appliances: Whirlpool Cooktop '22, Whirlpool Microwave '20, Whirlpool Wall Oven '20, Bosch Dishwasher '19, LG French door Fridge '19. ~ Steel Beam installed to Open Kitchen to Family room '22 ~ PGT IMPACT SLIDERS '22, IMPACT WINDOWS & DOORS '18, IMPACT Insulated GARAGE DOOR '18, Whirlpool Dryer '21, Hot Water Tank '21, and Samsung Washer '18 ~ Terrazzo Floors Redone '18-'20. Also Blinds '18-'20, Interior & Exterior Light Fixtures, Electrical Switches & Ceiling Fans replaced '19-'22, Interior Painted '18, Porcelain Plank Tile Floor '18 ~ Exterior Freshly Painted '20, Gutters, Fascia & Soffits '20-'21 ~ New 200 Amp Electrical Panel '20 ~ POOL: Pool Pump & Pool Filter 2020, Pebble Tec Pool Resurfaced '18, Pool Deck resealed '18, '23. New Pool Cage '21. ~ [Replacement of pipe off water meter with PVC, Replace Pipe from House to Street and Re-plumbed Overhead w/CPVC prior to '17] ~ Fencing '22, Landscaping & Irrigation '18-'25 ~ There is room to expand garage and Much More ~ LOCATION: Desirable Gulf Gate Estates has sidewalks, is well lit and has enforced deed restrictions to keep the properties nice. The low HOA $75/year is voluntary. This Modernized home is minutes away from World Renowned Siesta Beach and Legacy Trail, A+ Schools, Gulf Gate Library, the Gulf Gate Shops & Fine Restaurants. UTC Mall and Cultural Downtown are 20 minutes away. Just over 3 miles to Costco, an upcoming Whole Foods & Trader Joes. Enjoy the Florida Lifestyle in this wonderful South Sarasota Community that is quiet but minutes to everything. Make this updated home yours today ~ Not in Flood Zone.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Gina Larouche (941-323-0256)
1701 SOUTHWOOD ST #1701, SARASOTA, FL 34231
$260,000215 Days on yellowkey MLS ID: A4671475
REDUCED by $5,000 (1.9%) on 03/31/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1164 Built: 1981Monthly Fee: $1,273 Tax: $3,371 (2024)Community: Baywood ColonySpa: NoCondo
Taxes:$3,371
Tax Year: 2024
Remarks: RECENT PRICE ADJUSTMENT - MOTIVATED SELLERS! Rare Opportunity in Prestigious West of the Trail - Welcome to an exceptional corner residence just steps from the Intracoastal Waterway, nestled within the highly desirable Baywood Colony Southwood community. This beautifully updated 2-bedroom, 2-bath end unit is filled with natural light, enhanced by an abundance of windows complemented with elegant plantation shutters throughout. The front screened lanai has been fully enclosed with sliding glass panels and additional plantation shutters, creating a stylish and versatile space ideal for year-round enjoyment. Inside, the home presents like a model, featuring a stunning open-concept kitchen with granite countertops, a generous breakfast bar, stainless steel appliances, and premium soft-close wood cabinetry accented by under-cabinet lighting. A washer and dryer are conveniently located inside the residence, and elegant tile flooring extends throughout. Major improvements provide peace of mind, including a new A/C system (2018), a roof replacement by the HOA (2019), and a recently re-plumbed building. This ground-floor unit offers the added convenience of a covered parking space directly behind the residence, along with a secondary private entry from the carport. Residents enjoy an exceptional Florida lifestyle with access to a heated saltwater pool, tennis and pickleball courts just steps away, and tranquil walks to the Baywood Colony fountain—perfect for taking in spectacular bayfront sunsets. With only 32 residences, the community offers a rare sense of privacy and boutique-style living. The location is unbeatable: just 2.2 miles from beach access with an easy bike ride, and within walking distance to Phillippi Estate Park—a picturesque 60-acre waterfront preserve offering kayaking, fishing, scenic trails, a playground, a weekly Wednesday farmers market, and a variety of community events including art fairs and concerts. This pet-friendly, maintenance-free community includes basic cable, exterior and grounds maintenance, roof and window coverage, and pest control—all included in the low monthly fee of $1,273. Best of all, the community is not age-restricted. Experience the perfect blend of comfort, convenience, and coastal elegance in this truly special Sarasota residence.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Jo James, Llc (941-928-3175)
5543 ASHTON WAY #5543, SARASOTA, FL 34231
$275,00090 Days on yellowkey MLS ID: N6143396
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1232 Built: 1993Monthly Fee: $315 Tax: $3,561 (2025)Community: Ashton Lakes 8Spa: YesCondo
Taxes:$3,561
Remarks: Welcome to this charming 2 bedroom, 2 bath walk up condominium in the highly desirable Ashton Lakes community. This light and bright residence features high ceilings that create a spacious and open feel throughout the home. Enjoy relaxing on the screened lanai while taking in peaceful lake views and the natural beauty of the surroundings. The comfortable floor plan includes a spacious primary bedroom with a walk in closet and private ensuite bath, creating a quiet and inviting retreat. The guest bedroom is conveniently located near the second bathroom and can easily serve as a guest room or home office. Additional features include an inside laundry room and an assigned carport. Ashton Lakes is set on 33 acres of beautifully maintained grounds with four scenic lakes and offers a resort style lifestyle with a wide range of amenities. Residents enjoy two heated swimming pools, including one large pool with a lap lane, tennis courts, pickleball courts, shuffleboard courts, grilling areas, and a welcoming clubhouse that hosts an active social calendar during the winter season. The community is connected by a convenient footbridge to Merchants Mart shopping center where you will find CVS, Ace Hardware, a liquor store, Dollar Store, and the popular Detwiler’s Farm Market. Ideally located just 3.5 miles from the world famous Siesta Key Beach, this home also offers easy access to I 75 and US 41. Shopping, dining, schools, and hospitals are all within a short drive. The condominium fee includes cable TV, internet, water, trash, exterior and grounds maintenance, and an on site manager, providing convenience and peace of mind. Whether you are looking for a winter retreat or a full time residence, this lake view condominium offers a wonderful opportunity to enjoy the Florida lifestyle in a prime and convenient location.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rick Tritschler, Jr. (941-928-1292)
5811 CAVANO DR, SARASOTA, FL 34231
$565,00027 Days on yellowkey MLS ID: R4911277
0 Days Off yellowkey (back on 5/31/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1639 Built: 2014Monthly Fee: $287 Tax: $3,523 (2025)Community: Esplanade By Siesta KeyVilla
Taxes:$3,523
Remarks: One or more photo(s) has been virtually staged. Location, Location, Location — Minutes to world-famous Siesta Key Beach and all that culturally rich Sarasota offers: Theater, Van Wezel Performing Arts Hall, Ringling Museum to mention a few, fine and casual dining, Main Street shopping, UTC Mall, Legacy Trail, SRQ airport, hospital, and I-75. This attractive, split-plan 2-bedroom + den, 2-bath villa sits in Esplanade by Siesta Key a gated, maintenance-free community with resort-style amenities: heated zero-entry pool with lap lane, heated spa, pickleball, tennis, bocce, grass volleyball/badminton court, firepit, fitness center, community room with kitchen, fenced dog park and full-time property manager. HOA covers exterior maintenance, landscaping and roof care. The open great room plan flows to a screened, extended lanai with water views — perfect for entertaining, sunsets and bird watching. Primary suite features an ensuite bath with built-in shower bench, private water closet, dual-sink granite vanity. Guest bedroom with ensuite bath. Dining room includes a custom mirrored buffet with upper and lower cabinetry. The den is ideal for a home office, library or craft room. Upgrades and interior highlights: Mohawk wood plank flooring, new carpeting in bedrooms, large tile in kitchen, baths and laundry, tray ceilings in living and dining rooms, crown molding, recessed lighting, granite bath counters, Corian kitchen counters with integrated sink, tile backsplash with listello tile accent, custom kitchen and laundry cabinets (laundry includes utility sink), custom bedroom closets, ceiling fans, custom garage storage, plantation shutters, hurricane panels and security system. Located on a cul-de-sac with an extra long paver driveway. ALL information is believed to be accurate, but must be verified by the buyer and the buyer's agent* Don’t miss this dream home in Sarasota.
Listing is courtesy of: JOSELLE D. CULP (941-374-1274)
Listing Agent: Joselle Culp (941-374-1274)
5381 PALOS VERDES DR, SARASOTA, FL 34231
$1,299,000157 Days on yellowkey MLS ID: A4677221
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1956 Built: 1952 Tax: $7,868 (2025)Community: River ForestSingle Family
Taxes:$7,868
Remarks: Exceptional waterfront living on Phillippi Creek. This is a boater’s paradise with rare, unobstructed access to Phillippi Creek. This exceptional waterfront property offers 202 feet of solid seawall with no mangroves, expansive water views, and the privacy of a tucked-away cul-de-sac location. With ample space to park a boat or RV and a long private driveway, this home is perfectly suited for those who value both convenience and a true Florida waterfront lifestyle. A paver brick entry welcomes you to this Spanish Mediterranean–style residence, highlighted by a striking curved front door and timeless architectural details throughout. Inside, the open floor plan features tile flooring, graceful archways, wood crown molding, and wood beams in the living room. Large windows and sliding glass doors fill the home with natural light while framing stunning views of Phillippi Creek. The kitchen is designed for both functionality and entertaining, offering granite countertops, a large breakfast bar, custom cabinetry, and a spacious butler’s pantry. A separate laundry room includes built-in cabinetry for additional storage. The primary suite features sliding glass doors leading outdoors, creating a seamless connection to the waterfront setting. Step outside to enjoy a lagoon-style pool and the tranquil sights and sounds of the creek, ideal for relaxing or hosting guests. With direct water access, generous outdoor space, and a peaceful yet central location just minutes from Siesta Key, downtown Sarasota, and central Sarasota, this is a rare opportunity to own a private waterfront retreat with exceptional boating access and enduring architectural appeal. All information provided by the sellers is deemed reliable but is not guaranteed. Buyers are encouraged to verify all information independently.
Listing Agent: Reeny Kaney (941-954-5454)
2414 VACCARO DR, SARASOTA, FL 34231
$969,000158 Days on yellowkey MLS ID: A4677299
REDUCED by $14,000 (1.4%) on 05/29/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2330 Built: 2014Monthly Fee: $570 Tax: $6,350 (2025)Community: Esplanade By Siesta KeySingle Family
Taxes:$6,350
Remarks: NEW PRICE Best Value in the Neighborhood. Motivated sellers bring all offers. Live the Florida lifestyle. Located behind the gates of the sought-after Esplanade by Siesta Key, a beautifully appointed 3-bedroom, 3-bath residence with den and extended lanai, showcasing the highly desirable Lazio VII floor plan with tranquil water views. Curb appeal is enhanced by a striking stone façade, an expansive paver driveway, and lush landscaping supported by an automated sprinkler system with reclaimed water—along with ground maintenance, all included in the HOA. Step inside to discover an open-concept design ideal for both entertaining and everyday living, highlighted by new luxury vinyl flooring throughout main living area. The casual yet elegant kitchen is the heart of the home, featuring upgraded cabinetry with hidden hinges, decorative dentil molding, soft-close sliding drawers, granite countertops, a large gathering island, stainless steel appliances, double ovens, and a natural gas cooktop. This home offers three newly updated bathrooms, thoughtfully designed for modern living with high-end finishes and outstanding features. Additional upgrades include Low-E double-pane windows for energy efficiency, hurricane shutters, and Kevlar hurricane panels for the lanai and front door, providing peace of mind and easy storm preparedness. Recent improvements include new exterior waterproof paint, a new A/C system with UV light, a whole-house carbon water filtration system, and a reverse osmosis system under the kitchen sink. Elegant architectural details abound, including tray ceilings, tall interior doors, plantation shutters, and crown molding. The spacious primary suite features an oversized walk-in closet with custom built-in cabinetry.Perfectly situated just minutes from premier shopping, dining, and world-class entertainment—and only a short drive to the powdery sands of Siesta Key Beach—this meticulously maintained home offers luxury, comfort, and location in one remarkable package
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-556-2150)
Listing Agent: Ellen Wilson (704-651-6322)
1622 KENILWORTH ST, SARASOTA, FL 34231
$3,495,000169 Days on yellowkey MLS ID: A4676310
REDUCED by $205,000 (5.5%) on 04/30/2026
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 4058 Built: 2017 Tax: $28,823 (2025)Community: Johnson EstatesSpa: YesSingle Family
Taxes:$28,823
Remarks: Located West of Trail near the historic Field Club, this stunning residence is a refined interpretation of British West Indies architecture, offering over 4,000 square feet of thoughtfully designed single-level living. Set on an estate lot, the home blends timeless coastal elegance with exceptional craftsmanship and seamless indoor–outdoor flow. A dramatic great room welcomes you with vaulted wood ceilings, fireplace, and expansive pocketing sliders that frame views of the lushly landscaped pool and spa. The open-concept design flows effortlessly into the chef’s kitchen, appointed with premium Thermador and Wolf appliances, custom solid-wood cabinetry, quartz surfaces, and an oversized island—perfectly complemented by a separate dining area and custom dry bar with wine refrigeration. Designed for both privacy and versatility, the residence features four en-suite bedrooms, office, and a spacious TV lounge or bonus room that opens directly to the outdoor living areas. The private primary suite is a serene retreat with a vaulted wood ceiling, dual walk-in closets, and direct access to the covered lanai. Its spa-inspired bath showcases dual vanities, a soaking tub, and an expansive glass-enclosed shower. Outdoor living is a true centerpiece, with a generous travertine lanai, fully equipped outdoor kitchen, dining verandah, and a large gas- and electric-heated saltwater pool and spa with waterfall—ideal for entertaining or quiet relaxation amid tropical landscaping and architectural lighting. Additional highlights include hurricane-rated impact windows and doors, a whole-house generator, brand new metal roof, dual on-demand water heaters, an expansive paver motor court, low maintenance & fenced yard, and a rare four-car garage configuration, including an owner’s garage with EV outlet and climate control. Ideally located minutes from Siesta Key, Southside Village, Sarasota Bay, and downtown Sarasota, this exceptional home offers privacy, design integrity, and proximity to the best of the Sarasota lifestyle
Listing is courtesy of: ALLEN REAL ESTATE SERVICES INC (941-923-7777)
Listing Agent: John Allen, Pa (941-923-7777)
1475 LANDINGS CIR #43, SARASOTA, FL 34231
$629,00024 Days on yellowkey MLS ID: A4694471
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2040 Built: 1982 Tax: $674 (2025)Community: Landings TreehouseTownhouse
Taxes:$674
Remarks: There's no place quite like it in Sarasota. Tucked into the canopy of a lush, jungle-like landscape at The Landings, this three-story Treehouse townhome delivers the rare combination of absolute privacy and natural beauty that defines one of the Gulf Coast's most beloved communities. Soaring above the native palms and mossy oaks, this 2,040 sq ft, 3-bedroom, 2-bath + powder room residence has been thoughtfully updated while preserving the treetop retreat feeling that makes these homes so coveted. The 2025 renovated kitchen features fresh cabinetry and all-new washer and dryer ? move-in ready with nothing to do but settle in and listen to the breeze. A wood-burning fireplace anchors the living space with warmth and character, while multiple decks off each level bring the outdoors in at every turn. A private garage, generous lanai, and verdant views from nearly every window complete the picture. Exterior maintenance is included, so the only thing on your to-do list is enjoying it. And for those who travel with four-legged family members ? pets are welcome here with no weight restrictions. The Landings is a gated waterfront community offering residents access to Har-Tru tennis courts, a community pool, and the private Landings Yacht, Golf & Tennis Club (optional membership). All just minutes from world-class dining, the arts, and the sugar sands of Siesta Key. This is more than a home ? it's a lifestyle hiding in plain sight.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Judy Greene (941-350-0451)
5544 DINAH LN, SARASOTA, FL 34231
$1,895,00030 Days on yellowkey MLS ID: A4693403
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4433 Built: 1995 Tax: $9,270 (2025)Community: Terra Bea SubSingle Family
Taxes:$9,270
Middle School: Sarasota Middle
Remarks: You’ll love entertaining guests and embracing the tranquility of waterfront living in this one-of-a-kind classic Key West home on Philippi Creek Bayou. Enter through mahogany doors to soaring cathedral ceilings that fill the home with natural light and create an open, airy atmosphere. Expansive water views can be enjoyed in most rooms, while the outdoor deck provides the perfect setting to relax and take in stunning sunset skies. Inside, the Key West coral fireplace, luxury vinyl plank flooring and thoughtful architectural details create warmth and character throughout. The kitchen is designed for gathering and entertaining, featuring stainless steel appliances, a stainless-steel chef’s cooking area, quartz countertops and a wraparound bar that encourages memorable moments with family and friends. The enormous primary suite serves as a private retreat with its own water-view balcony, charming gas fireplace and bay windows. The spa-inspired en suite bath offers dual vanities and a relaxing spa tub. Dedicated office space provides flexibility for working from home or creating a quiet study area for the kids. Upstairs, you’ll find four bedrooms, a balcony and two full baths. The lower level features an expansive entertaining area ideal for a growing family, game room, gym or play space, along with a convenient pool bath for hosting guests. Outside, enjoy the private open pool area positioned at the water’s edge with long, peaceful canal views. The waterfront lifestyle continues with a kayak launch, Jet Ski floats and a newer composite boat dock with a 13,000-pound lift ready for boating adventures. Adding even more appeal for boating enthusiasts, the county is currently dredging the canal to further improve water access and navigation. The home has also been thoughtfully updated with a newer roof and freshly repainted interior and the property has been well maintained with no known storm-related damage or water intrusion. Just minutes from Philippi Shores Elementary and Riverview High School, this exceptional property is ideal for a growing family that loves the outdoors. A treasured Suncoast oasis where privacy, comfort and waterfront living come together beautifully.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Thomas Hedge, Jr (941-587-6660)
3361 CROSS CREEK DR #3361, SARASOTA, FL 34231
$277,50093 Days on yellowkey MLS ID: A4685552
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1027 Built: 1984Monthly Fee: $632 Tax: $2,667 (2025)Community: Crooked Creek Sec 7Condo
Taxes:$2,667
Elementary School: Wilkinson Elementary
Remarks: Welcome to one of the best locations in Crooked Creek! This beautifully updated first-floor 2 bedroom, 2 bath split-plan condominium is ideally situated in the building directly next to the heated pool and just steps from the private community gate leading into the stunning Red Bug Slough Preserve. Light, bright, and open, the residence features expansive floor-to-ceiling windows that bring the outdoors in, showcasing peaceful views of Crooked Creek, a charming footbridge, and lush Florida landscaping filled with native foliage and wildlife. Enjoy your morning coffee or evening beverage from one of two serene lanais surrounded by nature. The Interior has been COMPLETELY UPDATED IN 2021, and now has a BRAND NEW A/C UNIT just installed May 2026. This stunning home offers a MODERN UPDATED KITCHEN with solid surface counters, stylish cabinetry, updated appliances, recessed and under-cabinet lighting, along with new laminate and tile flooring throughout. Both BATHROOMS were BEAUTIFULLY RENOVATED, and the home also features fresh interior paint, plantation shutters, and recessed lighting in the kitchen, dining area, and guest bedroom. The versatile guest room includes a Murphy bed with built-in desk, making it perfect for visitors or a convenient home office. Crooked Creek residents enjoy numerous community improvements including NEW ROOFS (2019-2021), CARPORTS, EXTERIOR PAINT (2025), RESURFACED HEATED POOL (2025), and an updated poolside COMMUNITY KITCHEN (2025). Each unit includes covered parking and a private storage locker in a large community shed. Outdoor amenities include a heated pool, large pool deck with covered pergolas. A gazebo area with gas grills for BBQ gatherings, and a tennis/ pickleball court. Designed by RENOWNED ARCHITECT TIM SEIBERT of Sarasota School of Architecture, the Crooked Creek community is thoughtfully nestled within nature, with winding paths and tranquil surroundings that make it a true hidden gem. A must-see for nature lovers seeking peaceful Florida living just moments from everything Sarasota has to offer.
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Phyllis Coviello (941-408-3265)
1804 N LAKE SHORE DR, SARASOTA, FL 34231
$4,995,000145 Days on yellowkey MLS ID: A4679067
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 6854 Built: 2004 Tax: $22,275 (2025)Community: Oyster Bay EstatesSingle Family
Taxes:$22,275
Remarks: A residence of sophistication and luxury, this exceptional home was thoughtfully designed to bring family and friends together—sharing good food, meaningful connection, and the enjoyment of elevated everyday living. Ideally located just 8 miles from Sarasota-Bradenton International Airport, 12 minutes to Siesta Key Beach, and 10 minutes to downtown Sarasota, the property is in close proximity to The Ringling, Van Wezel, Selby Gardens, Asolo, premier dining and shopping, The Field Club, and the Sarasota Yacht Club—creating a seamless blend of culture, convenience, and coastal lifestyle. Elegant yet warm and approachable, the home blends refined architecture with tropical elements, including stone columns, metal pergolas, concrete textures, and lush landscaping, creating a relaxed oasis unlike any other. A surrounding stucco wall enhances privacy, allowing you to unwind to the soothing sound of a tranquil fountain within a peaceful, secluded setting. The main living spaces were intentionally designed for gathering, featuring bead-board stained ceilings in the family room, formal living room, and dining area. The cook’s kitchen is both striking and highly functional, highlighted by a glazed pressed-tin ceiling, unpolished concrete floors, and views into the kitchen garden through multiple French doors and expansive windows—perfectly suited for both everyday living and entertaining.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Bridget Spiess (941-720-6304)
3332 THORNWOOD RD #3332, SARASOTA, FL 34231
$278,000157 Days on yellowkey MLS ID: A4675963
REDUCED by $10,000 (3.5%) on 05/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1450 Built: 1981 Tax: $3,848 (2025)Community: Crooked Creek Sec 1Condo
Taxes:$3,848
Remarks: Hidden Gem Near Siesta Key! Incredible opportunity to own a beautifully UPDATED___TURN-KEY___ FIRST-FLOOR___ 2BR/2BA residence in the highly desirable Crooked Creek community at an exceptional value. Buyers will be hard-pressed to find this level of updates, community financial strength, and Sarasota location at this price point. Backing to the stunning Red Bug Slough Preserve, enjoy peaceful nature views, walking trails, fishing, biking, and tropical surroundings just minutes from Siesta Key Beach, shopping, dining, and downtown Sarasota. MOVE-IN READY with major updates completed from 2021-2025 including NEW A/C, water heater, appliances, impact windows/sliders, recessed lighting, ceiling fans, updated baths, tile flooring throughout, and enclosed Florida Room with floor-to-ceiling impact glass creating additional bright living space. No projects, no deferred maintenance—just move in and enjoy. Crooked Creek is a financially strong, meticulously maintained community of only 78 residences with FULLY FUNDED reserves and HOA fees that have actually DECREASED. Major community improvements already completed include NEW roofs, resurfaced heated pool, replaced carports, paved private roads, painted buildings, and beautifully maintained grounds. Future improvements are already scheduled and paid for. Community amenities include heated pool, tennis/pickleball, gazebo, grilling area, outdoor shower, storage locker, assigned covered carport, and ample guest parking. A rare combination of VALUE, LOCATION, UPDATES, and FINANCIAL STABILITY. This is the kind of property buyers wait for—and at this price, it is truly a MUST SEE.
2315 RIVERWOOD PINES DR, SARASOTA, FL 34231
$595,00017 Days on yellowkey MLS ID: A4695340
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2031 Built: 1973 Tax: $5,385 (2025)Community: Riverwood PinesSpa: NoSingle Family
Taxes:$5,385
Remarks: Welcome to this beautiful 4-bedroom, 2-bath pool home featuring an open-concept layout and numerous recent updates, including new flooring and a newer roof. This move-in-ready property offers a maintenance-free yard and is situated on a spacious oversized cul-de-sac lot with ample parking space for your cars, boats, toys, and guests. The home also features an oversized 2-car garage, a gorgeous dining area, and is being sold fully furnished, making it ideal as a primary residence, second home, or investment property. Located in a highly desirable school zone, this home is only a 12-minute drive to Siesta Key Beach, close to shopping and dining, and just 4.5 miles from Downtown Sarasota. With no HOA or CDD fees and no rental restrictions, this property offers endless flexibility and an incredible opportunity to enjoy the Florida coastal lifestyle. Bring your toys and start living the Florida dream today!
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Nikola Zafirovski (386-898-4335)
1624 STICKNEY POINT RD #101, SARASOTA, FL 34231
$450,00017 Days on yellowkey MLS ID: TB8511188
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1021 Built: 1975Monthly Fee: $992 Tax: $3,669 (2025)Community: Castel Del MareSpa: NoCondo
Taxes:$3,669
Elementary School: None
High School: None
Middle School: None
Remarks: Fully Remodeled Coastal Retreat – Move-In Ready & Just Steps from the Water! You must see this completely renovated, first-floor condo in beautiful Sarasota—offering effortless coastal living with a partial view of Little Sarasota Bay and just a short walk to the beach! This fully furnished, turn-key unit was completely gutted and redesigned in 2025, featuring high-end finishes and modern upgrades throughout. From the moment you walk in, you’ll notice the attention to detail as everything is brand new! Interior Highlights: Luxury LVP flooring throughout Brand new kitchen cabinets & stone countertops Brand new appliances Stylish modern light fixtures Spacious master bedroom with walk-in closet and door to screened in porch Master bath with stand-up shower & glass surround New vanities and toilets in both bathrooms New water heater Beautiful screened-in patio with new tile flooring Brand new hurricane proof sliding glass door to patio and windows throughout the unit Step outside your door and enjoy the convenience of ground-floor living in building 3, with tennis and pickle-ball courts just steps away. Community Amenities Include: 2 swimming pools Tennis & pickle-ball courts Shuffleboard court Fishing pier/gazebo on the Intracoastal waterway Sidewalks throughout community Clubhouse On-site property management Community laundry facilities Located directly on the Intracoastal Waterway and only a few blocks from the beach, this condo offers the perfect blend of relaxation, recreation, and convenience. Whether you're looking for a primary residence, vacation getaway, or investment opportunity, this one checks all the boxes. Don’t miss your chance to own a brand-new coastal condo in one of Sarasota’s most desirable locations!
Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)
Listing Agent: Stephen Hachey (813-642-6030)
7860 HOLIDAY DR, SARASOTA, FL 34231
$950,00048 Days on yellowkey MLS ID: A4691644
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2196 Built: 1957 Tax: $7,241 (2025)Community: Holiday HarborSingle Family
Taxes:$7,241
Remarks: Wonderfully charming street along HIDDEN HARBOR MARINA high and dry this lovely turn key home has 3 beds and 2.5 baths, a heated pool and large fenced yard.. NO HOA Country restrictions only Sarasota County restrictions. Home has many updates including a light and bright kitchen, window treatments, a king bed en-suite bath with French doors to a covered patio with plenty of lounging furniture and TV set up. This home comes turnkey furnished and has IMPACT RESISTANT, ENERGY EFFICIENT WINDOWS AND SLIDERS and a newer metal roof. You will love this HIDDEN HARBOR neighborhood with plenty of charm. Minutes to Siesta Key shopping and dining. A new shopping area to be completed by 2026 includes a new WHOLE FOODS and TRADER JOES as well as shopping and dining.
Listing is courtesy of: ROSEBAY INTERNATIONAL REALTY, INC (941-366-7673)
Listing Agent: Marianne Lebar (941-650-0337)
7294 CLOISTER DR #9, SARASOTA, FL 34231
$189,50045 Days on yellowkey MLS ID: A4691156
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 941 Built: 1987 Tax: $2,077 (2025)Community: Carrington PlaceCondo
Taxes:$2,077
Remarks: Welcome home to this first floor, stylishly updated 2-bedroom, 2-bathroom condo showcasing contemporary elegance throughout! This well-maintained and functional floor plan offers a comfortable living space with a cozy dining area, all highlighted by sleek tile flooring that flows seamlessly from room to room. The modernized kitchen is truly a standout, perfect for any home chef, with updated finishes and thoughtful design. Both bathrooms have been tastefully renovated with chic features and finishes, adding to the home’s overall appeal. With its open layout and abundance of natural light, this condo feels bright, inviting, and move-in ready! Enjoy the serenity of your private screened-in back patio....an ideal spot for morning coffee or unwinding in the evening. Carrington Place is a quaint, well-kept community featuring a lovely pool for residents to enjoy. Centrally located, you’re just minutes from the world renowned Siesta Key Beach, as well as a wide variety of shopping and dining options. For those with an active lifestyle, you’re also close to Legacy Trail! Perfect for biking, running, or walking. Schedule your showing today and come see all this beautiful condo has!
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Andrea Capek (941-497-6060)
5936 ALBERT PL, SARASOTA, FL 34231
$355,00060 Days on yellowkey MLS ID: O6399746
REDUCED by $5,000 (1.4%) on 05/30/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1018 Built: 1953 Tax: $3,588 (2026)Community: Stickney Point ParkSingle Family
Taxes:$3,588
Tax Year: 2026
Remarks: Tastefully renovated pool home located minutes to Siesta Key. This 2 bed 2 bath home has an additional room currently used as a third bedroom off of the living room. The other 2 bedrooms are separate ends of the home for added privacy. Minutes to many fine restaurants, local attractions and more. Can be sold as a package deal with #06398108,#06399737, #06399693, #06399686, #06398095
Listing is courtesy of: FRAKES REALTY (508-717-2752)
Listing Agent: Derek Frakes (508-717-2752)
5917 OLIVE AVE, SARASOTA, FL 34231
$473,00017 Days on yellowkey MLS ID: O6411402
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1330 Built: 1957 Tax: $3,209 (2025)Community: Golden AcresSingle Family
Taxes:$3,209
Remarks: One or more photo(s) has been virtually staged. Located in the desirable coastal community of Sarasota, this inviting home offers a relaxed Florida lifestyle with a comfortable layout and bright, open living spaces. The interior features a functional flow designed for everyday living and easy entertaining, with well-sized bedrooms and versatile common areas. Outdoor space provides room to enjoy the warm weather year-round, whether relaxing, gardening, or hosting gatherings. Conveniently situated near Gulf beaches, shopping, dining, and cultural attractions, this property delivers both lifestyle and location in one of Sarasota’s most sought-after areas.
Listing is courtesy of: MAINSTAY BROKERAGE LLC (800-583-2914)
Listing Agent: Raquel Littlejohn (470-279-6333)
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